Organosilicon compound, surface treatment agent, and resin additive

Abstract

To provide an organosilicon compound excellent in heat resistance and adhesion to a metal surface and capable of imparting corrosion resistance to the metal surface.SOLUTION: An organosilicon compound represented by the following formula (1): (In the formulae, R1's each independently represent hydrogen atoms, alkyl groups having 1 to 10 carbon atoms, or aryl groups having 6 to 10 carbon atoms, R2's each independently represent alkyl groups having 1 to 10 carbon atoms or aryl groups having 1 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, m represents an integer of 6 to 10, and n represents an integer of 1 to 3.). ) SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an organosilicon compound, a surface treatment agent, and a resin additive. [Background technology]

[0002] For the purpose of preventing metal rust, development of chromium-free (non-chromate) metal surface treatment agents is underway to replace chromium-based surface treatment agents such as toxic chromate and chromate phosphate.

[0003] Patent Documents 1 and 2 propose the use of imidazole ring-containing organosilicon compounds and benzotriazole ring-containing organosilicon compounds as surface treatment agents for metals, etc., but the corrosion resistance, adhesion, etc., of these compounds are insufficient.

[0004] Furthermore, Patent Document 3 discloses a metal surface treatment agent containing a silane coupling agent having a benzotriazole ring and a urea bond. The benzotriazole ring and the urea bond form a coordinate bond to form a sparingly soluble complex, thereby exhibiting rust prevention properties, and the hydrolyzable silyl group provides excellent processing adhesion. However, there is room for improvement in heat resistance, corrosion resistance, and adhesiveness. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2000-297093 [Patent Document 2] Japanese Patent Application Publication No. 6-279463 [Patent Document 3] Japanese Patent Application Laid-Open No. 2016-79130 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an organosilicon compound that has excellent heat resistance and adhesion to metal surfaces and can impart corrosion resistance to metal surfaces, as well as a surface treatment agent and a resin additive that contain this organosilicon compound. [Means for solving the problem]

[0007] As a result of extensive research to achieve the above object, the present inventors have discovered that a specific organosilicon compound has excellent heat resistance and adhesion to metal surfaces and can impart corrosion resistance to metal surfaces, thereby completing the present invention.

[0008] That is, the present invention provides: 1. An organosilicon compound represented by the following formula (1): [ka] (In the formula, R 1 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms; R 2 each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 1 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, m is an integer of 6 to 10, and n is an integer of 1 to 3. 2. The organosilicon compound of 1, wherein X is a group selected from the following formulas (2) to (6): [ka] (In the formula, R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and the wavy line represents a bond to an adjacent atom. 3. The organosilicon compound of 1, wherein m is 8. 4. A surface treatment agent containing any one of the organosilicon compounds of 1 to 3. 5. A resin additive containing any one of the organosilicon compounds of 1 to 3. 6. Articles whose surface has been treated with any of the organosilicon compounds listed in 1 to 3 to provide. [Effects of the Invention]

[0009] The organosilicon compound of the present invention has a structure in which a nitrogen-containing heterocycle is bonded to a silicon atom via a long-chain alkylene, and therefore exhibits good rust prevention performance due to the formation of coordinate bonds and hydrophobicity on the metal surface, as well as excellent adhesion and heat resistance. The organosilicon compound of the present invention having such characteristics does not contain chromium, and therefore can be suitably used as a surface treatment agent for various materials, such as a surface treatment agent for metals, or as a resin additive. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will be specifically described below. [Organosilicon compounds] The organosilicon compound of the present invention is represented by the following formula (1).

[0011] [ka]

[0012] In formula (1), R 1 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. R 1 The alkyl group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 1 to 6 carbon atoms may be linear, branched, or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, and cyclohexyl groups. Specific examples of the aryl group having 6 to 10 carbon atoms, preferably 6 to 8 carbon atoms, include a phenyl group and a tolyl group. Among these, R 1 is preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom.

[0013] R 2each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and the alkyl group having 1 to 10 carbon atoms and the aryl group having 6 to 10 carbon atoms are each represented by R 1 Among these, a methyl group is preferred.

[0014] X represents a monovalent group having a nitrogen-containing heterocycle, which may be a heteroaromatic ring or a partially or fully saturated heterocycle, and may have either a monocyclic structure or a polycyclic structure (including a spirocyclic structure). The nitrogen-containing heterocycle may further contain an oxygen atom and / or a sulfur atom in the ring. Specific examples of the nitrogen-containing heteroaromatic ring include pyrrole, maleimide, imidazole, pyrazole, pyrazolone, triazole, tetrazole, pyridine, pyridone, pyrazine, pyrimidine, pyridazine, triazine, tetrazine, azepine, diazepine, oxazole, isoxazole, thiazole, thiazolinone, isothiazole, isothiazolinone, furazan, oxadiazole, oxazine, oxadiazine, oxazepine, oxadiazepine, thiadiazole, thiazine, thiazepine, thiadiazepine, indole, isoindole, indolizine, indazole, pyrindine, quinoline, isoquinoline, quinolizine, purine, phthalazine, pteridine, naphthyridine, quinoxaline, quinazoline, cinnoline, benzoxazole, benzothiazole, benzimidazole, benzofurazan, benzothiadiazole, and benzotriazole rings.

[0015] Specific examples of partially or fully saturated nitrogen-containing heterocycles include pyrroline, pyrrolidone, pyrrolidine, pyrrolizidine, succinimide, imidazoline, imidazolidine, imidazolidone, triazoline, triazolidine, tetrazoline, tetrazolidine, pyrazoline, pyrazolidine, pyrazolidone, dihydropyridine, tetrahydropyridine, piperidine, piperidone, dihydropyrazine, tetrahydropyrazine, piperazine, dihydropyrimidine, tetrahydropyrimidine, perhydropyrimidine, dihydropyridazine, tetrahydropyridazine, and paclitaxel. -hydropyridazine, triazinane, triazinanetrione (isocyanuric acid), dihydroazepine, tetrahydroazepine, perhydroazepine, dihydrodiazepine, tetrahydrodiazepine, perhydrodiazepine, dihydrooxazole, tetrahydrooxazole (oxazolidine), dihydroisoxazole, tetrahydroisoxazole (isoxazolidine), dihydrothiazole (thiazoline), tetrahydrothiazole (thiazolidine), thiazolidinone, dihydroisothiazole (isothiazoline), tetrahydroisothiazo dihydrooxadiazole (isothiazolidine), isothiazolidinone, dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole, tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine, tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine, dihydrooxazepine, tetrahydrooxazepine, perhydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine, perhydrooxadiazepine, dihydrothiadiazole, tetrahydrothiadiazole (thiadiazolidine), dihydrothia Azine, tetrahydrothiazine, dihydrothiadiazine, tetrahydrothiazepine, tetrahydrothiazepine, perhydrothiazepine, dihydrothiadiazepine, tetrahydrothiadiazepine, perhydrothiadiazepine, morpholine, thiomorpholine, indoline, isoindoline, dihydroindazole, perhydroindazole, dihydroquinoline, tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline, tetrahydroisoquinoline, perhydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,Examples of such an alkyl group include perhydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline, tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline, perhydroquinazoline, dihydrocinnoline, tetrahydrocinnoline, perhydrocinnoline, dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole, perhydrobenzoxazole, dihydrobenzothiazole, perhydrobenzothiazole, dihydrobenzimidazole, and a perhydrobenzimidazole ring.

[0016] Specific examples of spiro-bonded bicyclic nitrogen-containing heterocycles and bridged bicyclic nitrogen-containing heterocycles include azaspiro[4.4]nonane, oxazaspiro[4.4]nonane, azaspiro[4.5]decane, oxazaspiro[4.5]decane, azabicyclo[2.2.1]heptane, azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, azabicyclo[2.2.2]octane, and azabicyclo[2.2.2]octane rings.

[0017] Among these, nitrogen-containing heteroaromatic rings containing neither oxygen nor sulfur atoms are preferred, and imidazole, benzimidazole, triazole (1,2,3-triazole or 1,2,4-triazole), and benzotriazole rings are more preferred.

[0018] That is, the above X is preferably a group selected from the following formulas (2) to (6).

[0019] [ka] (In the formula, the wavy lines represent bonds to adjacent atoms.)

[0020] In the formula, R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms. R 3The alkyl group having 1 to 12 carbon atoms may be linear, branched, or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl groups. Specific examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a tolyl group, and a xylyl group.

[0021] Specific examples of X include, but are not limited to, the following:

[0022] [ka] (In the formula, the wavy lines represent bonds to adjacent atoms.)

[0023] m represents an integer of 6 to 10, preferably an integer of 8 to 10, and more preferably 8. If m is less than 6, the heat resistance and rust prevention properties are insufficient, and if m exceeds 10, the content of heterocycles per unit mass decreases, which may result in a decrease in rust prevention properties and adhesiveness. n represents an integer of 1 to 3, with 2 or 3 being preferred from the viewpoint of adhesiveness.

[0024] The organosilicon compound represented by the above formula (1) can be obtained, for example, by reacting (A) an organosilicon compound containing a halogenated alkyl group (hereinafter referred to as compound (A)) with (B) a nitrogen-containing heterocyclic compound (hereinafter referred to as compound (B)) in air or in an inert gas atmosphere such as nitrogen.

[0025] Specific examples of compound (A) include 6-chlorohexyltrimethoxysilane, 6-chlorohexyltriethoxysilane, 6-bromohexyltrimethoxysilane, 6-bromohexyltriethoxysilane, 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 8-bromooctyltrimethoxysilane, 8-bromooctyltriethoxysilane, 8-bromooctyldimethoxymethylsilane, 8-bromooctyldiethoxymethylsilane, 10-chlorodecyltrimethoxysilane, 10-chlorodecyltriethoxysilane, 10-bromodecyltrimethoxysilane, 10-bromodecyltriethoxysilane, etc. These can be used alone or in combination of two or more.

[0026] Among these, 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 10-chlorodecyltrimethoxysilane, and 10-chlorodecyltriethoxysilane are preferred, and 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, and 8-chlorooctyldiethoxymethylsilane are more preferred.

[0027] Specific examples of compound (B) include imidazole, 1-methylimidazole, 2-methylimidazole, 4-methylimidazole, 4(5)-ethylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-propylimidazole, 2-butylimidazole, 4-phenylimidazole, 2-phenylimidazole, 2-undecylimidazole, 4-methyl-2-phenylimidazole, 1,2,4-triazole, 1,2,3-triazole, 5,6-dimethylbenzimidazole, 2-ethyl-1H-benzimidazole, 2-methylbenzimidazole, 5-methylbenzimidazole, 2-nonylbenzimidazole, 2-phenylbenzimidazole, benzimidazole, benzotriazole, 5,6-dimethylazimidobenzene, and 5-methylbenzotriazole. These may be used alone or in combination of two or more. Among these, imidazole and benzimidazole are preferred.

[0028] The above reaction may be carried out in a solvent, if necessary, to the extent that the reaction is not inhibited. Examples of the solvent include aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and decane; ether solvents such as tetrahydrofuran and 1,4-dioxane; amide solvents such as formamide, dimethylformamide, and N-methylpyrrolidone; and aromatic hydrocarbon solvents such as benzene, toluene, and xylene.

[0029] The above reaction is an exothermic reaction, and side reactions may occur if the temperature becomes too high. Therefore, the reaction temperature during production is preferably 20 to 150°C, more preferably 30 to 130°C, and even more preferably 40 to 110°C. The reaction time for the above reaction is not particularly limited as long as it allows temperature control of the above-mentioned exothermic reaction and the reaction is completed within the time period, but is preferably 10 minutes to 24 hours, more preferably 1 to 10 hours.

[0030] [Surface treatment agent] The surface treatment agent of the present invention contains an organosilicon compound represented by the above formula (1), and is particularly suitable for use as a metal surface treatment agent. From the viewpoint of stability, the organosilicon compound represented by the above formula (1) is preferably contained in a concentration of 0.001 to 20 mass %, more preferably 0.005 to 10 mass %, relative to the surface treatment agent of the present invention.

[0031] The surface treatment agent of the present invention may further contain an organosilicon compound other than the organosilicon compound represented by the above formula (1). Other organosilicon compounds include amino group-containing organosilicon compounds, epoxy group-containing organosilicon compounds, and isocyanuric acid structure-containing organosilicon compounds, and among these, amino group-containing organosilicon compounds are preferred.

[0032] The amino group-containing organosilicon compound may be a compound having at least one amino group selected from the group consisting of a primary amino group, a secondary amino group, and a tertiary amino group, and an alkoxysilyl group. Specific examples thereof include 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, 8-aminooctyltrimethoxysilane, 8-aminooctyldimethoxysilane, 8-aminooctyltriethoxysilane, 8-aminooctylmethyldiethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxy ... Examples thereof include N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldiethoxysilane, N-(β-aminoethyl)-γ-aminooctyltrimethoxysilane, N-(β-aminoethyl)-γ-aminooctylmethyldimethoxysilane, N-(β-aminoethyl)-γ-aminooctyltriethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldiethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropylmethyldimethoxysilane.

[0033] Specific examples of epoxy group-containing organosilicon compounds include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. A specific example of an organosilicon compound containing an isocyanuric acid structure is tris(trimethoxysilylpropyl)isocyanurate.

[0034] When other organosilicon compounds are used, the ratio of the organosilicon compound represented by the above formula (1) to the other organosilicon compounds is not particularly limited, but from the viewpoints of storage stability and productivity, the ratio of the other organosilicon compounds to 1 mole of the organosilicon compound represented by the above formula (1) is preferably 0.1 to 100 moles, more preferably 0.5 to 20 moles, and even more preferably 1 to 10 moles.

[0035] The surface treatment agent of the present invention may further contain water, an organic solvent, or both as a solvent. From the viewpoint of the stability of the composition, it is preferable to use water adjusted to be acidic. Examples of acids used to adjust the acidity include organic acids such as formic acid, acetic acid, and citric acid; and inorganic acids such as hydrochloric acid. When an acid is used, the amount added is preferably 0.001 to 0.5 mass %, more preferably 0.01 to 0.2 mass %, of the total surface treatment agent. When an acid is used, the water may be adjusted to be acidic by mixing the acid with water in advance, or the acid may be added to a surface treatment agent containing water to adjust the acidity.

[0036] The organic solvent is not particularly limited, but examples thereof include methanol, ethanol, isopropanol, n-butanol, diacetone alcohol, ethylene glycol, ethyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, N,N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, methyl ethyl ketone, and methyl isobutyl ketone, and these may be used alone or in combination of two or more.

[0037] [Resin additives] The organosilicon compound represented by the above formula (1) can be added to various resins either alone or as a composition containing the organosilicon compound and the above-mentioned solvent, etc., to impart adhesion and rust prevention properties to metal surfaces. Examples of the resin include silicone resin, vinyl chloride resin, acrylic resin, phenol resin, epoxy resin, polycarbonate resin, and polybutylene terephthalate resin. The amount of the organosilicon compound represented by the above formula (1) is preferably 0.001 to 20% by mass, more preferably 0.005 to 10% by mass, based on the resin. [Example]

[0038] EXAMPLES The present invention will be explained in more detail below by showing examples and comparative examples, but the present invention is not limited to these examples.

[0039] [1] Synthesis of organosilicon compounds [Example 1-1] A 1L separable flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 102.12g (1.5mol) of imidazole and 500g of dimethylformamide. 81.03g (1.5mol) of sodium methoxide was added while stirring at 10°C, and the mixture was heated to 120°C. 403.28g (1.5mol) of 8-chlorooctyltrimethoxysilane was added dropwise, and the mixture was stirred at 120°C for 3 hours. The reaction was then terminated by confirming complete disappearance of the imidazole peak by gas chromatography (GC). Distillation was then performed to obtain a pale yellow liquid organosilicon compound represented by the following formula (7).

[0040] [ka]

[0041] [Example 1-2] The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 333.57 g (1.5 mol) of 2-undecylimidazole, to obtain a pale yellow liquid organosilicon compound represented by the following formula (8).

[0042] [ka]

[0043] [Examples 1-3] The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 103.61 g (1.5 mol) of 1,2,4-triazole, to obtain a pale yellow liquid organosilicon compound represented by the following formula (9).

[0044] [ka]

[0045] [Examples 1-4] The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 177.21 g (1.5 mol) of benzimidazole, to obtain a colorless, transparent liquid organosilicon compound represented by the following formula (10).

[0046] [ka]

[0047] [Examples 1-5] The same procedure as in Example 1-1 was carried out, except that imidazole in Example 1-1 was changed to 178.70 g (1.5 mol) of benzotriazole, to obtain a pale yellow liquid organosilicon compound represented by the following formula (11).

[0048] [ka]

[0049] [Comparative Example 1-1] The same procedure as in Example 1-1 was carried out, except that 8-chlorooctyltrimethoxysilane was replaced with 298.08 g (1.5 mol) of 3-chloropropyltrimethoxysilane, to obtain a pale yellow liquid organosilicon compound represented by the following formula (12).

[0050] [ka]

[0051] [Comparative Example 1-2] The same procedure as in Example 1-1 was carried out, except that in Example 1-1, imidazole was changed to 177.21 g (1.5 mol) of benzimidazole and 8-chlorooctyltrimethoxysilane was changed to 298.08 g (1.5 mol) of 3-chloropropyltrimethoxysilane, to obtain a pale yellow liquid organosilicon compound represented by the following formula (13).

[0052] [ka]

[0053] [2] Manufacturing of surface treatment agents [Examples 2-1 to 2-5, Comparative Examples 2-1 and 2-2] To a mixed solvent of 89.5 g of propylene glycol monomethyl ether and 9.5 g of a 0.1 mass % aqueous acetic acid solution, 1 g of each of the organosilicon compounds (7) to (13) obtained in Examples 1-1 to 1-5 and Comparative Examples 1-1 and 1-2 was added, and the mixture was stirred at room temperature for 60 minutes to obtain a surface treatment agent.

[0054] [3] Manufacturing of processed items A commercially available copper plate (KDS Corporation; 70 mm × 150 mm × 1 mm) was pretreated by immersing it in a 30% by mass H2SO4 aqueous solution for 30 seconds and then drying it. Next, the pretreated copper plates were immersed for 5 minutes in the surface treatment agents obtained in Examples 2-1 to 2-5 and Comparative Examples 2-1 and 2-2, and then dried at room temperature for 60 minutes to obtain test plates. The heat resistance and corrosion resistance of the obtained test plates were evaluated according to the following evaluation methods. The results are shown in Table 1.

[0055] (1) Heat resistance evaluation The test plate was heat treated in an oven at 150°C for 30 minutes, and then the appearance was visually evaluated as follows: ○: No discoloration ×: Discoloration (2) Evaluation of corrosion resistance The obtained test plates were subjected to a salt spray test based on JIS Z 2371:2015 for 50 hours and 100 hours, after which the corroded area was measured and the corrosion resistance was evaluated according to the following method. A: Corrosion area is 0% B: Corrosion area is between 0% and 30% C: Corrosion area is 30% or more but less than 50% D: Corrosion area is 50% or more but less than 70% E: Corrosion area is 70% or more

[0056] [Table 1]

[0057] As shown in Table 1, the test plates of Examples 2-1 to 2-5 are superior in heat resistance and rust prevention (corrosion resistance) to those of Comparative Examples 2-1 and 2-2.

[0058] [4] Production of resin composition [Examples 3-1 to 3-5, Comparative Examples 3-1 and 3-2] Resin compositions were prepared by adding 0.5 mass % of each of the organosilicon compounds (7) to (13) obtained in Examples 1-1 to 1-5 and Comparative Examples 1-1 and 1-2 to a silicone resin (KR-251 manufactured by Shin-Etsu Chemical Co., Ltd.).

[0059] The adhesive properties of the resulting resin compositions were evaluated by the following method, and the results are shown in Table 2. (3) Evaluation of adhesiveness A commercially available copper plate (KDS Corporation; 70 × 150 × 1 mm) was pretreated by immersing it in a 30% by mass H2SO4 aqueous solution for 30 seconds and then drying it. The resin compositions obtained in Examples 3-1 to 3-5 and Comparative Examples 3-1 and 3-2 were applied to the pretreated copper plate using a bar coater 5, and dried at 25°C for 60 minutes to obtain a test plate with a coating film formed on the copper plate. The obtained test plate was immersed in boiling water at 100°C for 1 hour, and then a cross-cut test with 25 squares was carried out in accordance with JIS K5600-5-6:1999, and the presence or absence of peeling of the coating film was evaluated on the following three-point scale. ⊚: No peeling was observed. ○: Peeling is observed in some areas. ×: All peeled off.

[0060] [Table 2]

[0061] As shown in Table 2, it can be seen that the coating films made of the resin compositions of Examples 3-1 to 3-5 have superior adhesion compared to those of Comparative Examples 3-1 and 3-2.

Claims

1. An organosilicon compound represented by the following formula (1): 【Chemistry 1】 (In the formula, R 1 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms; R 2 each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 1 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, m is an integer of 6 to 10, and n is an integer of 1 to 3.

2. 2. The organosilicon compound according to claim 1, wherein X is a group selected from the following formulas (2) to (6): 【Chemistry 2】 (In the formula, R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and the wavy line represents a bond to an adjacent atom.

3. 2. The organosilicon compound according to claim 1, wherein m is 8.

4. A surface treatment agent comprising the organosilicon compound according to any one of claims 1 to 3.

5. A resin additive comprising the organosilicon compound according to any one of claims 1 to 3.

6. An article whose surface has been treated with the organosilicon compound according to any one of claims 1 to 3.

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